1. Field of the Invention
The present invention relates to novel 3-halo-5-halomethyl-2-oxazolidinones and to the method of their preparation. This invention also relates to methods of use of these compounds as microbicides.
2. Discussion of the Related Art
A large number of commercial, industrial, agricultural, and wood products are subject to microbiological attack which reduces or destroys their economic value. Examples of materials that may be subject to microbiological degradation are surface coatings, wood, agricultural seed, leather and plastics, including flexible plastics.
The temperature at which these products are stored and their intrinsic characteristics make these products susceptible to the growth of microorganisms. These microorganisms can be introduced during the manufacturing of these products by exposure to air, tanks, pipes, equipment, and humans and/or during their use from multiple openings and reclosures of packaged products and by the introduction of contaminated objects to stir or remove material.
Aqueous systems containing organic materials are also highly subject to microbiological attack. Such aqueous systems include latexes, surfactants, dispersants, stabilizers, thickeners, adhesives, starches, waxes, proteins, emulsifying agents, detergents, cellulose products, agricultural irrigation fluids, and resins formulated in aqueous solutions, emulsions or suspensions.
These systems frequently contain relatively large amounts of water causing them to be well-suited environments for microbiological growth and, thus, attack and degradation. Microbiological degradation of aqueous systems containing organic materials may manifest itself as a variety of problems, such as loss of viscosity, gas formation, objectionable odors, decreased pH, emulsion breaking, color change, and gelling.
Another objectionable phenomenon occurring in industrial process systems involving water is slime formation. Slime consists of matted deposits of microorganisms, fibers and debris. It may be stringy, pasty, rubbery, tapioca-like, or hard, and may have a characteristic undesirable odor that is different from that of the liquid suspensions in which it is formed.
The microorganisms primarily involved in slime formation are different species of spore-forming and nonspore-forming bacteria, in particular capsulated forms of bacteria which secrete gelatinous substances that envelop or encase the cells. Slime microorganisms also include filamentous bacteria, filamentous fungi of the mold type, yeasts, and yeast-like organisms. Slime reduces yields in paper production and causes plugging and other problems in water systems.
In addition, different types of water both potable and nonpotable need disinfectants to keep them from being spoiled by microorganisms. In the United States, the most common method of disinfection is the use of chlorination.
Chlorination, however, can be accompanied by some disadvantages, such as chlorine gas explosion or leakage, during water treatment, and may result in the formation of toxic halocarbons, such as chloroform and others In this respect, a variety of compounds are used as replacements for chlorine treatment, including ozone, chlorine dioxide, bromine, potassium permanganate, p-chlorosulfamidobenzoic acid, cyanuric acid derivatives, isocyanuric acid derivatives, quaternary ammonium compounds, and various chloramine compounds, such as 3-chloro-4,4-dimethyl-2-oxazolidinone, which are disclosed in U.S. Pat. No. 4,000,293.
Substituted oxazolidinones containing N-halogen are known compounds. They are described in U.S. Pat. Nos. 3,591,601; 4,000,293, 4,659,484 and 4,954,151 as well as other patents and literature. To the inventors' knowledge, 3-halo-5-halomethyl-2-oxazolidinones are not known in the art.
Walles, in U.S. Pat. No. 3,591,601, describes compounds of the general formula: ##STR1## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 can be lower alkyl or hydrogen and X can be either bromine or chlorine. Kaminski, in U.S. Pat. No. 4,000,293, specifically includes compounds where R.sup.1 and R.sup.2 are lower alkyl groups and R.sub.3 and R.sub.4 are hydrogens or R.sup.1 and R.sup.2 are hydrogens and R.sup.3 and R.sup.4 are lower alkyl groups. Kaminski claims that it is essential for these compounds to have either a 4- or 5-quaternary carbon to be useful as disinfectants (Col. 2, lines 54-58).
Most of the researchers in this field consider that germinal alkyl groups are required for the use of N-Halo oxazolidinones as disinfectants. However, the present inventors have surprisingly found that 3-halo-2-oxazolidinones having a halomethyl substituent at the 5-position can provide long term disinfectant effectiveness.
As can be seen in the description provided above of the known compounds, neither of the above patents disclosed or suggested either the preparation or use of 3-halo-5-halomethyl-2-oxazolidinones. As is described below, particularly in Examples 1 and 2, these compounds can be prepared from readily available starting materials. In addition, the 5-halomethyl group in these compounds can provide an additional source of halogen for additional and lasting disinfectant activity of these compounds.